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The 10 Best Vacation Rentals in Islamorada, USA

Check out our selection of great vacation rentals in Islamorada

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Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest Price First Star rating and price Top reviewed

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The villa with a terrace and pool views features 2 bedrooms, 2 living rooms, a flat-screen TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the villa. The property has an outdoor dining area.

loved the location and the quick responses from the host.

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9
Wonderful
24 reviews

This air-conditioned holiday home has 2 bedrooms and 2.5 bathrooms, a cable flat-screen TV, and a fully equipped kitchen. The holiday home also provides a bathroom with a shower.

The holiday home includes a barbecue. There is a a terrace at this property and guests can go snorkelling, fishing and diving nearby. Two kayaks and 2 bicycles are offered. A boat hire is available for a surcharge.

Location perfect. Right in the middle of Islamorada. Grounds are beautiful and well maintained. Great view of the ocean from the pool. The pool was great. Clean and large. Bathrooms by the pool is a great touch. The house was large and beautiful and clean and well furnished. Fantastic neighborhood. Could not have chosen a better place to stay.

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9.2
Wonderful
24 reviews

Situated 1.9 km from Sea Oats Beach, Matecumbe Resort offers 2-star accommodation in Islamorada and has a private beach area, an outdoor swimming pool and a garden. This beachfront property offers access to table tennis, free private parking and free WiFi. The property offers allergy-free units and is located 9.2 km from Upper Matecumbe Key.

wow booked last minute, right on the little beach , beautiful views from windows, everything you need.

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8.5
Very Good
325 reviews
Price from
$175
per night

Situated in Islamorada and only 3.8 km from Windley Key, EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS features accommodation with sea views, free WiFi and free private parking. This holiday home offers a private beach area, a garden, as well as a tennis court. The property features a year-round outdoor pool with a pool bar and is set 9.1 km from Upper Matecumbe Key.

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8.5
Very Good
2 reviews
Price from
$129.38
per night

The spacious holiday home with a balcony and sea views features 2 bedrooms, a living room, a TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area.

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Price from
$181.07
per night

Set in Islamorada, 1.1 km from Sea Oats Beach and 10 km from Upper Matecumbe Key, Beachfront Villa at Islamorada BY THE GLAMHOMES offers a private beach area and air conditioning. This beachfront property offers access to a balcony, free private parking and free WiFi. On clear days, guests can head outside to enjoy the villa's outdoor fireplace or simply kick back and relax.

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Price from
$1,530
per night

Set in Islamorada, 1.2 km from Sea Oats Beach and 2.2 km from Anne's Beach, Plaza Del Sol offers air-conditioned accommodation with a terrace and free WiFi. This holiday home features accommodation with a balcony. The property is non-smoking and is situated 13 km from Upper Matecumbe Key.

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The holiday home features 2 bedrooms, a TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area.

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The spacious holiday home has 6 bedrooms, 6 bathrooms, bed linen, towels, a TV with cable channels, a dining area, a fully equipped kitchen, and a balcony with sea views. Guests can take in the ambience of the surroundings from an outdoor dining area or keep themselves warm by the fireplace on colder days. For added privacy, the accommodation features a private entrance.

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The spacious holiday home features 6 bedrooms, a TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 5 bathrooms with a walk-in shower. Towels and bed linen are provided in the holiday home. The property has an outdoor dining area.

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Price from
$508.21
per night

Most booked vacation rentals in Islamorada this month

Enjoy breakfast in Islamorada!

  • Anglers Reef Getaway
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 24 reviews

    Offering an outdoor swimming pool and a garden, Anglers Reef Getaway in Islamorada is close to Windley Key and Windley Key Fossil Reef Geological State Park.

    The amenities,the location, the villas and the pool

  • Anglers Reef Paradise
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 26 reviews

    Anglers Reef Paradise is located in Islamorada, 984 feet from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi.

    perfektes Südstaatenfeeling sehr exquisit und sicher

  • Matecumbe Resort
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 326 reviews

    Matecumbe Resort features a public bath and air-conditioned accommodations in Islamorada, 1.2 miles from Sea Oats Beach.

    El lugar es súper bonito! Y es Perfecto para la familia

  • Tollgate Tides
    Breakfast options

    Just a 6-minute walk from Anne's Beach and one mile from Sea Oats Beach, Tollgate Tides features accommodations in Islamorada with a garden.

  • Beachfront Villa at Islamorada BY THE GLAMHOMES

    Providing an outdoor swimming pool, Beachfront Villa at Islamorada BY THE GLAMHOMES offers accommodations in Islamorada.

  • Plaza Del Sol
    Breakfast options

    Plaza Del Sol is located in Islamorada, just 1.4 miles from Anne's Beach and 8.2 miles from Upper Matecumbe Key. This vacation home features accommodations with a balcony.

  • Two White Turtles

    Two White Turtles offers accommodations in Islamorada, 21 miles from Florida Keys Aquarium Encounters and 21 miles from Pigeon Key.

  • Waterfront Wonder

    Waterfront Wonder is located in Islamorada, just 1.5 miles from Anne's Beach and 7.6 miles from Upper Matecumbe Key. Guests may go for a swim in the private pool.

These vacation rentals in Islamorada have options with FREE cancellation

  • Casa Koto
    Free cancellation options available

    Casa Koto offers accommodations in Islamorada, a 13-minute walk from Sea Oats Beach and 1.4 miles from Anne's Beach. This beachfront property offers access to a balcony and free Wifi.

  • Sun-kissed Bliss
    Free cancellation options available

    Sun-kissed Bliss offers accommodations in Islamorada, a few steps from Sea Oats Beach and a 19-minute walk from Anne's Beach.

  • EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 2 reviews

    EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS in Islamorada provides accommodations with a private beach area, an outdoor swimming pool, and a garden.

  • Paradise Beach
    Free cancellation options available

    Paradise Beach offers accommodations in Islamorada, a few steps from Sea Oats Beach and 1.2 miles from Anne's Beach. This beachfront property offers access to free Wifi.

FAQ about vacation rentals in Islamorada






Vacation Rentals That Guests Love in Islamorada

  • Avg. price/night: $325.13
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 820 reviews
    The layout and I like that’s acomplete boutique hotel unique great staff and absolutely great planned villas n rooms
    ventura
    Family with young children
  • Avg. price/night: $236.45
    7.0
    Scored 7.0
    Good
    Rated good
     · 1,235 reviews
    Our 2 storey pool villa was fabulous. Really liked the pool area and breakfast was nice in the lobby.
    Sarah
    Young couple
  • Avg. price/night: $325.13
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 820 reviews
    Upgraded to a villa! Beautiful spot to watch sunrise. Hot tub and two pools were lovely. Champagne complimentary on arrival. Very good restaurant next door. Good variety of foods at breakfast which you could eat at outdoor tables or take to your room. Villa very clean with a well equipped kitchen. All staff we encountered were very pleasant!
    Mason
    Young couple
  • Avg. price/night: $245.26
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,043 reviews
    The villa we stayed in was terrific, facing the ocean and the pool. The property was quiet. Definitely not fancy or upscale, but had all the basics, except there wasn't much space to move between the bed and the bathroom. Not sure if the rooms in the main building were as nice as the villa.
    Bonnie
    Young couple
  • Avg. price/night: $245.26
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,043 reviews
    great location. had ocean view villa. nice amenities. staff was good. didn’t bother you unless asked. there is no beach to smit at in property but many state parks w beaches close by. this place is not busy and was very relaxing.
    A
    Anonymous
    Young couple
  • Avg. price/night: $420.75
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 838 reviews
    Our villa was beautiful with ocean views. The place was immaculate and spacious , the staff was so nice and accommodating. We had a wonderful stay.
    Gia
    Group
  • 9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 7 reviews
    I loved the fact that we could all be together on vacation, but have our own separate villas. Each villa (#103 & 116) was beautiful, well appointed and immaculate. 116 had a big yard with fire pit, deck, lawn furniture, picnic table and a corn hole set which was perfect for family get togethers.
    Sara
    Family with young children
  • Avg. price/night: $245.26
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,043 reviews
    The Villa had 2 double beds, patio and an ocean view. The place was clean and the staff was very friendly.
    Fleming
    Group
  • 9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 24 reviews
    super private and quiet community. Villa was spacious and had all the amenities. the pool was gorgeous!
    Lindsay
    Family with young children
  • 9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 8 reviews
    This was our first time using booking.com and staying at Anglers Reef. Both were a success. I highly recommend Anglers Reef for a family friendly experience in paradise. The villa accomodations were wonderful and the host was very responsive to our questions. The pool, views of the water, beautiful palm trees, fishing/dock area, and cute villas exceeded our expectations. Also, it was a great location in the Keys for finding outdoor fun and great restaurants.
    Anthony
    Family with young children